I have a Core Data model similar to this:

When a Webgallery or Article object gets saved, it may use one or many pictures. They can use the same photographical subject but maybe in different sizes. I don’t save pictures that don’t get used in either a WebGallery or an Article.
Picture‘s relationships instance and social are set to cascade, so when the Picture object gets deleted, the corresponding PictureInstance and Social objects get deleted too.
1) Is there any way to know when a picture doesn’t get used anymore, neither by WebGallery nor by Article so it can be deleted?
2) Is it a problem that the relationships previewPicture and teaserPicture don’t have an inverse?
You should have an inverse for the relationship. With the inverse, the question becomes trivial. When a simple cascade rule will delete them from WebGallery and Article. (or perhaps you just want to nullify).
(Core Data Programming Guide)
You can simply check if a picture is used whenever you delete it from a gallery or article: